Sinteza in pretvorbe etil (E)-3-(fenilamino)akrilata

Edrovska, Iva (avtor), Svete, Jurij (mentor)

Enaminoni so spojine, ki vsebujejo amino skupino, ki je preko C=C dvojne vezi konjugirana s karbonilno skupino in so uporabni reagenti v sintezni organski kemiji kot prekurzorji za tvorbo različnih heterocikličnih sistemov. Reakcije enaminonov praviloma potekajo pod blagimi reakcijskimi pogoji in dajejo produkte z dobrimi izkoristki. V preteklosti so enaminone večinoma sintetizirali iz ketonov in aminov z reakcijo kondenzacije ali pa z reakcijo adicije aminov na elektronsko revne alkine (inone). Danes so znane tudi nove sintezne metode s poudarkom na principih zelene kemije. V okviru tega diplomskega dela smo poskušali sintetizirati enaminone, etil (E)-3-(alilamino)akrilat (73) in etil (E)-3-(fenilamino)akrilat (75), po modificiranem postopku iz literature. Izvajali smo reakciji Michaelove adicije anilina in alilamina na etil propiolat pri sobni temperaturi, brez topila in brez katalizatorja. V nadaljevanju smo zaščitili aminsko skupino v sintetiziranih enaminonih z uporabo reagenta Boc2O.

• Jezik: Slovenski jezik
• Ključne besede: enaminoni, amini, etil propiolat, Michaelova adicija
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2023
• PID: 20.500.12556/RUL-149138
• COBISS.SI-ID: 165439491
• Datum objave v RUL: 04.09.2023

EDROVSKA, Iva, 2023, Sinteza in pretvorbe etil (E)-3-(fenilamino)akrilata [na spletu]. Diplomsko delo. [Dostopano 14 april 2025]. Pridobljeno s: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=slv&id=149138

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Synthesis and conversions of ethyl (E)-3-(phenylamino)acrylate

Izvleček

Enaminones are compounds containing an amino group conjugated with a carbonyl group via a C=C double bond. Enaminones are of great importance in synthetic organic chemistry, since they can be used in the syntheses of various heterocyclic systems. Reactions of enaminones usually take place under mild reaction conditions and the products are obtained in good yields. Previously, enaminones were usually synthesised by the condensation reactions between ketones and amines or by addition reactions between amines and electron-deficient alkynes (ynones). Today, new synthetic methods with an emphasis on green chemistry principles are increasingly investigated. In this thesis we have attempted to synthesise two enaminones, ethyl (E)-3-(phenylamino)acrylate (75) and ethyl (E)-3-(allylamino)acrylate (73), via a modified literature procedure following the principles of green chemistry. We performed non-catalysed Michael addition reactions of aniline and allylamine to ethyl propiolate at room temperature, under solvent-free reaction conditions. Next, the amine groups of the synthesised enaminones were protected using Boc2O as the reagent.

• Ključne besede: enaminones, amines, ethyl propiolate, Michael addition